Methylene-disalicylic-acid derivative



Patented June 17, 1930 PATENT OFFICE SAMUEL LEWIS SUMMERS, OF FORT WASHINGTON, PENNSYLVANIA METHYLENE DISALICYLIG-ACID DERIVATIVE No Drawing.

My invention relates to organic compounds and their manufacture, and is especially concerned with a novel methylene-disalicyl amide diacetate or methylene-diacetyl-disalicyl amide, and its homologues such ashereinafter indicated. These substances (especially the particular one named) are useful for pharmaceutical purposes, as hereinafter indicated.

My product maybe prepared as follows: Starting with methylene-disalicylic acid, the first step is esterification. Various omologous esters may be produced in the man- 'ner hereinafter described,by using the corresponding methyl, ethyl, propyl, or other alcohols,with a corresponding difierence in the esterifica'tion product. A way of carrying out the esterification with ethyl alcohol is as follows:

Dissolve 288 lbs. of methyleneedisalicylic acid in 150 lbsuof ethyl alcohol, and slowly add to the solution, at a temperature of 70 C., a solution of 60 lbs 66 B. sulphuric acid N diluted with lbs. water. When this has all been added, raise the temperature to 150 C. under a reflux condenser, and hold at this temperature for about 2 hours. The essential product is the ester, methylene-diethyldisalicylate can omoomn omaomoomn amide, which may be done as follows:

This product, obtained as above described (or an equal amount prepared in any other suitable way), is heated with a solution of 210 lbs. of acetic anhydride dissolved in 100 The next main step is to acetylate this Application filed July 5, 1928. Serial No. 290,709.

lbs. of acetic acid. This heating iscarried out under a reflux condenser, and is continued for four hours. The essential product is my novel methylene-disalicyl amide diace'tate or methylene-diacetyl-disalicylamide having 5 the empirical formula clgHlgNgog and the structural formula: I

cm CH.

ONE: 3

000cm 4' ONE: 3"

It is a crystalline substance, insoluble in water and substantially tasteless, but soluble in alcohol and ether. It has valuable phar- 6 maceutical properties, being useful as anti;v neuralgic, anti-rheumatic and anti-arithritic. It is to be taken internally, the dosage being from 45 to 120 grains a day.

Having thus described my invention, I claim:

1. The hereindescribed methylene-diacetyldisalicyl amideyinsoluble in water and substantially tasteless, but soluble in alcohol and ether; and typified by the empirical formula CHI-113N206 2. The hereindescribed me'thylene-diacetyldisalicyl amide; insoluble in Water and substantially tasteless,but soluble in alcohol and ether; and having the formula vania, this 29th day of June, 1928.

SAMUEL LEWIS SUMMERS. 

